Senior Security Engineer, Offensive Security

## Responsibilities - Plan and execute red team engagements end-to-end, simulating real-world threat actors across cloud infrastructure (AWS, GCP), Kubernetes, CI/CD pipelines, and corporate environments - Build and maintain custom offensive tooling, automation frameworks, and engagement infrastructure, treating offensive operations as a software engineering problem - Develop custom payloads and evasion capabilities tailored to Datadog's environment and modern defensive controls (EDR, SIEM, network monitoring) - Improve the efficiency of offensive operations through thoughtful use of automation and AI, accelerating reconnaissance, vulnerability analysis, and reporting workflows - Partner with the Detection & Response team on purple team exercises to validate detection logic, improve alert fidelity, and influence threat models - Translate offensive findings into concrete improvements by working directly with defensive security and engineering teams to close gaps ## Requirements - You have 5+ years of hands-on experience in offensive security (red teaming, penetration testing, or adversary simulation) with a track record of operating against mature, well-defended environments - You write production-quality code (Python, Go, or similar), can build your own tools, and automate your workflows rather than relying exclusively on off-the-shelf frameworks - You have deep expertise in at least a two of the following areas: macOS security, Linux security, cloud platforms (AWS, GCP, Azure), Kubernetes, or CI/CD pipelines - You have experience developing evasion techniques against modern defensive controls and understand how detections work from the blue team side - You have strong communication skills, with the ability to convey complex offensive findings clearly and effectively to both technical and non-technical stakeholders - You are comfortable operating with ambiguity, scoping your own work, identifying what matters most, and driving projects from prototype to deployed and validated ## Nice to Have - Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you're passionate about technology and want to grow your skills, we encourage you to apply. ## Benefits - New hire stock equity (RSUs) and employee stock purchase plan (ESPP) - Continuous professional development, product training, and career pathing - Intradepartmental mentor and buddy program for in-house networking - An inclusive company culture, ability to join our Community Guilds (Datadog employee resource groups) - Free, global mental health benefits for employees and dependents age 6+ - Competitive global benefits